반응 #40611

반응 방정식

sodium bicarbonate

sodium thiosulfate

8-indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

3-chloroperoxybenzoic acid

→

title compound

수율 67.0%

8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

수율 67.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   추출the aqueous solution was extracted with CH2Cl2
4. 4
   세척The combined CH2Cl2 fractions were washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   기타Removal of the solvent and chromatography on silica
7. 7
   세척eluting with EtOAc/hexanes (1:3-1:1.6

실험 절차

To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.3 g, 0.79 mmol) in 5 mL of CH2Cl2, was added 3-chloroperoxybenzoic acid (m-CPBA, 69.5%, 431 mg, 1.73 mmol) portionwise. The solution was stirred at room temperature for 3 hours. An aqueous solution of 10% sodium thiosulfate was added to quench the reaction. After 30 minutes saturated sodium bicarbonate solution was added, and the aqueous solution was extracted with CH2Cl2. The combined CH2Cl2 fractions were washed with brine and dried over Na2SO4. Removal of the solvent and chromatography on silica, eluting with EtOAc/hexanes (1:3-1:1.6, v/v) gave 0.22 g (67%) of the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ (ppm): 9.75 (s, 1H), 8.70 (s, 1H), 7.39 (d, J=7.8 Hz, 1H), 7.24 (s, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.38 (q, 2H), 3.19 (s, 3H), 3.00 (m, 4H), 2.10 (m, 2H), 1.40 (t, 3H).

출처